I left the first man in Nice, at the base of the 213 steps leading up to the Colline du Château—Castle Hill, in English. We'd just spent three weeks backpacking through Spain, three weeks of sightseeing, sex, and whiskey con Coca-Colas, but when I turned to walk away from him that day, I knew in my gut our fun was over. "You go ahead," I told him, eyeing the straight vertical climb up the stone wall, his preferred route since the elevator went only three-quarters of the way. "I'll meet you at the hostel." There isn't a castle up there anyway, I harrumphed to myself, only the crumbling ruins of one. There was, however, a panoramic view of the harbor and the Riviera glittering like a diamond necklace. My companion wanted to see it.

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In the preceding weeks, we'd traveled from Madrid to Toledo, Córdoba, Seville, Granada, Ronda, Málaga, Marbella, then back up to Barcelona. We'd gone to bullfights and cathedrals and museums, sunbathed topless at beaches (or I did, anyway), and watched the moon rise from open-air bars. In Granada, we'd toured every inch of the Alhambra's sprawling Moorish splendor. In Barcelona, we'd ascended the winding, snail-like towers of the Sagrada Família

In Ronda, we'd picked our way down almost 300 steps from the Casa del Rey Moro to a fourteenth-century water mine at the bottom of a gorge. By the time we reached Nice, I felt like I'd climbed every goddamned set of stairs in Europe. Forget Myers-Briggs; I have a quicker test for couples: Are you always, unwaveringly, a stair person, or do you sometimes break down and take the elevator?

"You don't like adventure," my travel companion said, his athletic calf muscles clenching like fists as he turned to start his solo climb. It was the kind of meanspirited, airily diagnostic pronouncement one would issue to a sibling, a lover you'd begun to feel contempt for, or someone with whom you'd been sharing an upper train bunk for too many nights in a row. We were two out of three, and arguing like brother and sister: over finding ants in the bed of the Seville pensione, about the bowl of chocolate ice cream I'd cavalierly ordered from room service in Marbella. "You're no fun," he called back, in case I hadn't heard him the first time

He was a casual college boyfriend, a sweet, loping Texas kid from a comfortable upper-middle-class family to my intense Midwestern striver. I'd won a $7,500 academic prize for my thesis, and, on a lark, decided to use some of it to travel with him. Our bodies fit together nicely—I loved his tawny, smooth skin and strong hands—but sex and our alma mater, from which we'd graduated three weeks prior, were pretty much all we had in common. We were careful to avoid acknowledging this. I'd half-hoped this trip might clarify what we had not been able to determine for ourselves in the course of eight months together. But I suspected he wasn't quite as ambivalent as I was: He wanted me to meet his father, who was soon to arrive in France on a business trip.

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There, at the bottom of those steps, I knew I'd never meet his dad, that it would be pointless and disingenuous for me to do so. I made up a story that involved a girlfriend I wanted to see in Paris. After that, I remember sitting in an outdoor café, listlessly eating a thin, salty fish soup that might as well have been gruel, while the sky dimmed to an inky black and tourists shouted around me in a cacophony of foreign languages. I thought I would feel euphoric and vindicated—free!—but instead I just felt desolate and awful, like I was wearing a wet bathing suit on a warm, sunny day that had suddenly gone cold.

How fortuitous, then, that the great love of my 22 years happened to be in Milan, a mere eight hours by train from Nice. He was there setting up an office for an investment bank. This was the boyfriend with whom I'd been giddily in love for the first time in my adult life. He had a sharp, practical intelligence and was driven to an intoxicating, if sometimes intimidating, degree. When he'd broken up with me by phone the previous fall, saying he needed to "focus on his career," he'd left me with the emotional DTs: For meals, I stood storklike at the kitchen counter spooning ice cream from the pint. At night I read until the wee hours—I remember poring over Elizabeth Wurtzel's Bitch, underlining the names of women I wanted to emulate—and called the Psychic Friends Network to ask the disembodied voice on the other end if there was a chance that he and I might get back together. Someday? Maybe? If the stars aligned? Texas guy had been a diversion, a Vicodin in human form.

Back in Nice, I did what we did before cell phones: I bought a phone card and called my ex's New York office from a pay phone. His secretary gave me the number of his hotel. "Come meet me in Milan," he said. We had unfinished business; we both knew it. I was on a train the next morning.

The next three days in Milan were a blur of sensual pleasures. A fairytale sleep in the high-thread-count bed at the five-star Principe di Savoia— the draperied, mahogany, Art Deco wonderland his employer was paying for, and easily the fanciest hotel I'd ever set foot in. A transcendent dinner of gnocchi and red sauce in a restaurant tucked in the cozy downstairs of the proprietress's home. The fragrant, strong coffee that cleansed our palates after boozy meals of tannic red wine, and then woke us up again in the morning. The nearly unbearable sweetness of sex: We were still so in love.

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Yet it was all tinged with sadness as well. He'd long ago told me that he wouldn't make room for a relationship in his blinkered, cubicle-bound existence. But I didn't want to marry him! I wasn't in a rush to acquire a husband or children or the trappings of a domestic life. To put it in cultural perspective: I graduated from college the year after Ally McBeal became a cause célèbre and the same week Sex and the City first aired. I simply wanted someone with whom I could talk and laugh—and I wanted to sleep with him for the rest of my life. I needed to make him understand this.

I wasn't in a rush to acquire a husband or children or the trappings of a domestic life...I simply wanted someone with whom I could talk and laugh—and I wanted to sleep with him for the rest of my life. I needed to make him understand this.

On the third morning, as he stood in the bathroom, naked after sex, I got up from the bed, pulled on some underpants, positioned myself casually in the doorframe, and made the predictable but perpetually unwise move of initiating a "discussion." I soliloquized about my feelings, offering up all the platitudes of love. My Shakespearean speech was met with silence, followed by a long, loud flush.

"Did you know," he said, "that this bathroom has a bidet?" I'd just excavated my soul for him, and he was talking about the bidet. But I wasn't going to protest. I was too proud for that. In silence, I gathered up my dignity along with my clothes and offered a vague excuse about why I needed to leave. We shared a late lunch in a nearby courtyard, where I ate the platonic ideal of a ham-and-cheese panini— I think about it to this day—and then rolled my tiny suitcase to a cabstand. I wasn't sure where I was headed.

I took a train to Paris, a city I knew slightly from a high school summer as a foreign exchange student and a college summer spent researching my thesis. I checked into an affordable hotel where I'd previously stayed. And I bet you can guess what I did next: I called another man, one I'd dated briefly the previous fall.

When I began this essay, I oscillated between feeling an almost celebratory pride—in my youthful independence, in the blithe, confident way I owned my desires and my sexuality—and a perhaps antiquated fear that reading about a woman's sexual escapades might be unpalatable to some. As Kathryn Schulz wrote in a New York magazine profile of Wild author Cheryl Strayed, who spent a summer hiking 1,100 miles on the Pacific Crest Trail: "In a culture with profoundly ambivalent feelings about independent women, it is not always clear what kind of adventures we will be lauded for undertaking, nor what kind of tales we will be lauded for telling." Indeed, I also found myself struggling with the not unrelated formal challenge this subject matter presented. How to prevent it from reading like a desultory string of episodic affairs, devoid of plot or theme? How to write about a libidinous, wayward, searching character who behaves, some would say, like a bit of a scoundrel, but who also happens to be a woman?

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If I were to write this story as a book, it would be a picaresque novel: a first-person account of "the adventures of a rogue held together only by the personality of its hero," to quote the late Orville Prescott, erstwhile book critic for the New York Times, in his review of Saul Bellow's The Adventures of Augie March. In a picaresque tale—Augie March, Henry Fielding's Tom Jones, Mark Twain's Adventures of Huckleberry Finn, even Hunter S. Thompson's Fear and Loathing in Las Vegas, among many others—the protagonist tends to be an outsider of modest origins, a trickster, a social climber. He rambles around having adventures, some romantic, and getting into comedic scrapes. He has "no more morals than a tomcat," to quote Prescott again, and is eternally unrepentant.

Like these male antiheroes, I was a drifter of sorts during that strange, liminal summer after graduating from college: alone, deracinated, restless, without immediate goals or obligations, indifferent to consequences. "I think a lot of women live like this now, from adventure to adventure," my husband's ex-mother-in-law, a wild-child 1970s actress, told me when I ran into her and mentioned the essay I was writing. "I know I did," she said, laughing, "and I don't regret a minute of it."

And yet historically, there haven't been many female picaresque narratives. There's Daniel Defoe's Moll Flanders, a novel that purports to be the true account of a female criminal who thieves, prostitutes herself, and marries five times in her wily quest to avoid poverty. Fast-forward 250 years, and there's Erica Jong's 1973 Fear of Flying, the sexually candid story of a poet who, while on a business trip with her husband, meets another man and jaunts around Europe with him. There are a few other examples of female picaresques I could name, but the point is, it's as masculine a genre as there is. Which is not surprising: Only in the past few decades have women had the luxury of wandering alone through the world.

There haven't been many female picaresque narratives. It's as masculine a genre as there is. Which is not surprising: Only in the past few decades have women had the luxury of wandering alone through the world.

Of course, in the 1960s and '70s, feminists began challenging societal constraints, opening up new professional and personal possibilities for women. Now, in 2016, we're living in a different universe, one in which Eat, Pray, Love, Elizabeth Gilbert's memoir of traveling alone to Italy, India, and Indonesia, sells over 9 million copies and becomes a 2010 rom-com starring Julia Roberts. The massive recent success of both that book and Wild would seem to indicate that such stories reflect the truth of women's lives. Or maybe they speak to an appetite for no-strings adventure—the desire to experience it voyeuristically, if not in reality.

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Because even today, most women cannot take the kind of trips Gilbert and Strayed did. Most of us are bound by the usual exigencies of life, particularly after a certain age. Plus, as oldfashioned as it sounds, it's still more acceptable for a man to roam around alone than it is for a woman. This may be why both writers' adventures are incited by domestic upheaval: divorce and a failed rebound romance in Gilbert's case, divorce and the death of her mother in Strayed's. As Schulz puts it, "It is as if only the total destruction of the domestic sphere could justify a woman's presence on such adventures."

I decided to travel on my own because, as I told a friend the weekend we graduated, we were the freest we'd ever been and likely would ever be again. Looking back, my motivations are more obvious to me now than they were then. I was—what? Reveling in my freedom. Following my intuition and urges. Having sex. Having fun. Living like the men I'd read about in books.

The guy I called was a Wall Street executive I'd met during an internship the previous summer at an investment bank in New York City. I'd asked him to lunch as the relationship with my ex had begun to unravel. We spent a few lighthearted weekends together that fall before I became too engrossed in writing my thesis to see him.

He was eight years my senior, successful, witty. But he was also the son of a wealthy Southern family—he had a thick, caramelly drawl—and I glimpsed strains of traditionalism and conservatism poking up like weeds from beneath his affable, modern-dude demeanor. He bought me a navy-blue cashmere sweater at an upscale boutique because my own sweaters were pilling and chintzy. He corrected my table manners and my slouchy posture. At restaurants, he'd fussily unfold his napkin, placing it neatly on his lap, then arrange his silverware in military-straight lines. I used to neglect mine to antagonize him, waiting to see how long it would take him to say something. But I viewed these as minor quirks. He was charming. He made me laugh. I liked fucking him. You could say I made an international booty call.

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Looking back, my motivations are more obvious to me now than they were then. I was—what? Reveling in my freedom. Following my intuition and urges. Having sex. Having fun. Living like the men I'd read about in books.

Crazily enough, he flew from New York to Paris the next day. He booked us a room at a luxury hotel called the Hotel Square, which I remember as a monolithic gray stone building that loomed portentously on a street corner. "Le bâtiment gris, lá," I told the cabdriver as we pulled up, feeling sophisticated and a little louche to be giving him directions to the scene of my impending assignation. Inside, the decor was modern and subdued: gray curtains and gray bed linens on low-lying platform beds, black wooden furniture. There seemed to be bowls of macarons on every surface.

I waited in the room for him. Sprawled diagonally across the neatly made bed, I flipped through a French tabloid and ate pink and green macarons. Upon arriving, he gave me a quick, chaste kiss—"What're you eating, bonbons?" he said—set down his bag, and then proceeded to remove all his clothes and head for the shower. Afterward, he walked around the room naked, toweling his wet hair and retrieving things from his suitcase while his flaccid penis flopped around like a water balloon. Now, I was obviously not a prude, but his stripping startled me. Months had passed since we'd seen each other, let alone slept together. I hadn't realized it until that moment, but I'd expected him to sweep in and seduce me anew, to woo me with dinner, or at least a bottle of wine, before he undressed in front of me in the stark light of late morning. Or maybe I would've done the seducing, had he waited more than five minutes to denude himself. It was as though he viewed me as a quotidian piece of his life's furniture, like we were an old married couple of 60-odd years.

Or at least those were the thoughts that crossed my mind at the time. Who can fathom the fragile unpredictably of desire? Whatever the reason, I did not want to sleep with him. Not then. Not later. Not ever again in my life. I could only view him with a clinical detachment, instead of with the soft, idealizing light of amorous possibility. He'd return the favor, though, after he pressed himself against me in the bed that night, and I scooted to the opposite side, then avoided his overtures for the next 48 hours. Frustrated, he announced that I could stay in the Hotel Square for the rest of the week—he'd pay for it—but that he was leaving. "I hope you never do this to another man," he said, and I wish I could say I felt sorry for him.

With a 22-year-old's flair for theatrics, I ran after him through the tasteful lobby of the Hotel Square, down the street, and to a rental-car place where he paid for a tiny, pewter-colored Peugeot. "Where are you going?" I demanded. He wouldn't tell me. So I opened the car door and staged a sit-in in the passenger seat. "I'm coming with you," I told him. Seventeen years later, as someone who craves solitude, it's funny and perplexing to me that I didn't want to be left alone in an expensive hotel in Paris. Surely it was a mix of pride, boredom, a refusal to be rejected, and the terrifying vastness of my newfound freedom that made me insist on accompanying him.

We spent the next five days driving through the Loire Valley, touring the castles with a relentless intensity—Chenonceau, Chambord, Chinon, Amboise—and in total silence. He wouldn't speak to me, so after a while I gave up, replacing the sex we weren't having with chocolate mousse and multiple glasses of wine at meals.

In the end, this isn't a story of redemption, capped by a life-altering epiphany. It's not a fairy tale that culminates in my falling in love. The point is the adventure, just as it was the point of the trip itself.

This bizarre castle tour eventually built up the necessary erotic tension between us. One afternoon, I hammily sidled up to him as we looked at a faded old tapestry in a drafty castle; he burst out laughing. Suffice it to say, we made up. We drove back to Paris, where we said an amicable early-morning good-bye, and I checked myself into another cheap hotel.

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In the end, this isn't a story of redemption, capped by a life-altering epiphany. It's not a fairy tale that culminates in my falling in love. The point is the adventure, just as it was the point of the trip itself. Because let's face it, when I realized I wasn't into the guy from Texas, I could have called one of my sisters, or a girlfriend. But I didn't. And anyone who's ever traveled with someone they're attracted to will understand why. It's thrilling to stand next to that person and take in art and architecture and the grand monuments of history while an electrical current passes between you, and you can't wait to get back to your hotel. A sense of discovery, companionship, sex (and the frisson leading up to it), the utter lack of long-term plans: This is what solo travel is about. Sure, it can be about solitude, but it's also about opening yourself to new people and experiences. When you travel alone, you might call someone up and say, "Come see me." And when someone says, "Come to Italy," you might get on a train and go.